Synthesis of 11,12-Didehydrodibenzo[a,e]cycloocten-5(6H)-one: A Strained Eight-Membered Alkyne

被引:17
作者
Kornmayer, Stefan C. [1 ]
Rominger, Frank [1 ]
Gleiter, Rolf [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
来源
SYNTHESIS-STUTTGART | 2009年 / 15期
关键词
alkynes; cycloadditions; eliminations; oxidations; ring expansion; 1,5-CYCLOOCTADIYNE;
D O I
10.1055/s-0029-1217404
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
An eight-step synthesis of 11,12-didehydrodibenzo[a,e]cycloocten-5(6H)-one (10) was developed. The structure of 10 was assigned by spectroscopic means and confirmed by X-ray analysis of its 2,4-dinitrophenylhydrazone derivative. Reaction of the triple bond of 10 with dicarbonyl(eta(5)-cyclopentadienyl)cobalt or dicarbonyl(eta(5)-pentamethylcyclopentadienyl)cobalt gave the corresponding metal-stabilized cyclobutadiene complexes.
引用
收藏
页码:2547 / 2552
页数:6
相关论文
共 24 条
[1]
[Anonymous], MODERN ACETYLENE CHE
[2]
Brettreich M, 2002, ANGEW CHEM INT EDIT, V41, P3688, DOI 10.1002/1521-3773(20021004)41:19<3688::AID-ANIE3688>3.0.CO
[3]
2-Q
[4]
BRETTREICH M, 2002, ANGEW CHEM, V114, P3840
[5]
STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].
COREY, EJ ;
CHO, H ;
RUCKER, C ;
HUA, DH .
TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458
[6]
CRYSTAL-STRUCTURE OF 5,6-DIDEHYDRODIBENZO[A,E]CYCLO-OCTENE [J].
DEGRAAFF, RAG ;
GORTER, S ;
ROMERS, C ;
WONG, HNC ;
SONDHEIMER, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (03) :478-480
[7]
PREPARATION OF 1,5-CYCLOOCTADIYNE AND 1,3,5,7-CYCLOOCTATETRAENE FROM 1,5-CYCLOOCTADIENE [J].
DETERT, H ;
ROSE, B ;
MAYER, W ;
MEIER, H .
CHEMISCHE BERICHTE, 1994, 127 (08) :1529-1532
[8]
Synthesis and properties of 1,6,7,12,13,18,19,24-octamethylacenaphthylena [b, l] tetraphenylene [J].
Elliott, EL ;
Orita, A ;
Hasegawa, D ;
Gantzel, P ;
Otera, J ;
Siegel, JS .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (04) :581-583
[9]
Farrujia LJ., 1997, J APPL CRYSTALLOGR, V30, P565, DOI [10.1107/S0021889897003117, DOI 10.1107/S0021889897003117]
[10]
NEW, GENERAL-ROUTE TO FUNCTIONALLY SUBSTITUTED ETA5-CYCLOPENTADIENYL METAL-COMPOUNDS [J].
HART, WP ;
MACOMBER, DW ;
RAUSCH, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1196-1198